WO2012146889A1 - Composant de formulation - Google Patents

Composant de formulation Download PDF

Info

Publication number
WO2012146889A1
WO2012146889A1 PCT/GB2012/000341 GB2012000341W WO2012146889A1 WO 2012146889 A1 WO2012146889 A1 WO 2012146889A1 GB 2012000341 W GB2012000341 W GB 2012000341W WO 2012146889 A1 WO2012146889 A1 WO 2012146889A1
Authority
WO
WIPO (PCT)
Prior art keywords
adjuvant
agrochemical composition
benzoate
mesotrione
composition according
Prior art date
Application number
PCT/GB2012/000341
Other languages
English (en)
Other versions
WO2012146889A4 (fr
Inventor
Gordon Alastair Bell
Julia Lynne Ramsay
Raul Minguez MOLINA
David Stock
Gary Charles WALTER
Original Assignee
Syngenta Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Limited filed Critical Syngenta Limited
Priority to US14/113,678 priority Critical patent/US10206388B2/en
Priority to CN201280020196.XA priority patent/CN103491786B/zh
Priority to BR112013027279A priority patent/BR112013027279B8/pt
Priority to EP12716512.4A priority patent/EP2701518B1/fr
Priority to ES12716512T priority patent/ES2711639T3/es
Publication of WO2012146889A1 publication Critical patent/WO2012146889A1/fr
Publication of WO2012146889A4 publication Critical patent/WO2012146889A4/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
    • A01N45/02—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring having three carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • This invention relates to the use of aromatic esters as adjuvants in compositions, particularly for agrochemical use, as well to compositions comprising such an aromatic ester, in combination with at least one agrochemical and at least one surfactant.
  • the invention further extends to methods of making and using such compositions.
  • the present invention relates to such compositions when formulated as, or comprised by, an emulsion concentrate (EC), an emulsion in water (EW), a suspension of particles in water (SC), a microcapsule formulation (CS), a suspension of particles with an emulsion (SE), a dispersion concentrate (DC) or an oil suspension (OD).
  • EC emulsion concentrate
  • EW emulsion in water
  • SC suspension of particles in water
  • CS microcapsule formulation
  • SE suspension of particles with an emulsion
  • DC dispersion concentrate
  • OD oil suspension
  • An adjuvant is a substance which can increase the biological activity of and Al but is itself not significantly biologically active.
  • the adjuvant is often a surfactant, and can be included in the formulation or added separately, e.g. by being built into emulsion concentrate formulations, or as tank mix additives.
  • an adjuvant In addition to the effect on biological activity, the physical properties of an adjuvant are of key importance and must be selected with a view to compatibility with the formulation concerned. For instance, it is generally simpler to incorporate a solid adjuvant into a solid formulation such as a water-soluble or water-dispersible granule.
  • adjuvants rely on surfactant properties for biological activity enhancement and one typical class of adjuvants involves an alkyl or aryl group to provide a lipophilic moiety and a (poly)ethoxy chain to provide a hydrophilic moiety.
  • the present invention is based on the discovery that aromatic esters with relatively long hydrocarbon chains are surprisingly effective adjuvants, significantly enhancing the biological activity of active ingredients.
  • Aromatic esters of varied hydrocarbon chain lengths have until now only been known as solvents (such as Benzoflex 181TM and Finsolv®TN), emollients and thickening agents for use in various industries.
  • solvents such as Benzoflex 181TM and Finsolv®TN
  • emollients emollients and thickening agents for use in various industries.
  • solvents such as Benzoflex 181TM and Finsolv®TN
  • R is OH, halogen, or di-d. 4 alkyl amino
  • n is an integer selected from 0 to 20 inclusive
  • each A is independently Ci.i 0 alkanediyl
  • n is an integer selected from 1 , 2 and 3;
  • R 2 is selected from the group consisting of C 7 -C 2 c,alkyl, C 7 -C 20 alkenyl, C 7 -C 20 alkyldienyl and C 7 -C 2 o alkyltrienyl; and when m is 2 or 3, R 2 is selected from the group consisting of C C 2 o alkyl, C -C 22 alkenyl, C 4 -C 22 alkyldienyl and C 6 -C 22 alkyltrienyl; and
  • the invention provides for the use of an aromatic ester of formula (I) as described herein as an adjuvant in an agrochemical composition.
  • the invention provides for the use of an agrochemical composition as described herein to control pests.
  • a method of controlling a pest comprising applying a composition of the invention to said pest or to the locus of said pest.
  • an agrochemical composition as described herein, comprising combining an active ingredient, a surfactant and an aromatic ester of formula (I).
  • Alkyl groups and moieties are straight or branched chains, and unless explicitly stated to the contrary, are unsubstituted.
  • suitable alkyl groups for use in the invention are hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyi, tridec l, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl groups.
  • Alkenyl groups and moieties are straight or branched chains having a single carbon-carbon double bond, and unless explicitly stated to the contrary, are
  • alkenyl groups for use in the invention are hept-1- enyl, hept -2-enyl, hept -3-enyl, oct-1-enyl, non-1-enyl, dec-1-enyl, undec-1-enyl, and groups derived from monoenoic fatty acids including cis-4-decenyl, cis-9-decenyl, cis-5- laurolyl, cis-4-dodecenyl, cis-9-tetradecenyl, cis-5-tetradecenyl, cis-4-tetradecenyl, cis-9- hexadecenyl, cis-6-hexadecenyl, cis-6-octadecenyl, cis-9-octadecenyl, trans-9- octadecenyl,
  • Alkyldienyl groups and moieties are straight or branched chains having two carbon-carbon double bond, and unless explicitly stated to the contrary, are
  • alkyldienyl groups for use in the invention are hept- 1 ,3-dienyl, linoleyl, and linoelaidyl.
  • Alkyltrienyl groups and moieties are straight or branched chains having three carbon-carbon double bond, and unless explicitly stated to the contrary, are
  • alkyldienyl groups for use in the invention hex-1 ,3, 5-trienyl, hepta-1 ,3,5-trienyl, and linolenyl.
  • alkanediyl defines bivalent straight or branch chained hydrocarbon radicals such as, for example, methylene, 1 ,2-ethanediyl, 1, 1-ethanediyl, 1 ,3- propanediyl, 1 ,1-propanediyl, 1,2-propanediyl, 1 ,4-butanediyl, 1 ,5-pentanediyl and the like.
  • halogen includes F, CI, Br, and I, with fluorine and chlorine being particularly preferred halogens.
  • fluorine and chlorine being particularly preferred halogens.
  • the preferred values for m, n, and q, as well as the preferred groups for R 1 and R 2 , in any combination thereof (unless specifically stated otherwise) are as set out below.
  • R 1 may be a hydroxyl group, a halogen, or a di-C ⁇ alkyi amino group wherein each alkyi is independently C C alkyi.
  • R 1 is a di-Ci-C 4 alkyi amino group, and in particular a di C C 4 alkyi amino group wherein each alkyi group is independently methyl, ethyl, propyl or butyl, more preferably methyl or ethyl, and most preferably each alky group is methyl.
  • R 1 is hydroxy, preferably 2-hydroxy.
  • R 1 is preferably at the 4 position of the phenyl ring. In certain embodiments it is preferred that q is 0.
  • each A is independently a C1-C10 alkanediyl group.
  • each A is independently a C1-C4 alkanediyl group, more preferably each A is
  • each A is independently 1 ,2-ethanediyl, 1 ,2-propanediyl, 1 ,2-butanediyl, or 1,4- butanediyl. 1 ,2-ethanediyl is most preferred.
  • n is an integer selected from 0 to 20 inclusive.
  • n is an integer selected from 0-10 inclusive, more preferably 0-5 inclusive, even more preferably n is 0, 1 , 2, or 3, and most preferably n is 0, or 1.
  • m 1 , 2 or 3.
  • R 2 is H, or C 7 -C 20 alkyi. More preferably in such embodiments R 2 is C 8 -C 18 alkyi, more preferably C 8 -Ci5 alkyi, and more preferably still, Ci 2 -C 15 alkyi. In specific embodiments when m is 1 , R 2 is 2-ethyl hexyl, C 12 alkyi, C13 alkyi, d 4 alkyi, C 15 alkyi, C 16 alkyi, C 17 alkyi, oleyl or isoocatadecyl.
  • each R ⁇ q, A and n is independently as defined hereinbefore, furthermore, each group
  • R 2 is independently attached to any carbon atom in R 2 , and R 2 is Ci-C 2 o alkyl. In certain of ast a C 2 alkyl group, and each group
  • R 2 is C 7 -C 18 aikyi, more preferably, C 8 - C 17 alkyl, more preferably C 8 alkyl, C 12 -Ci 5 alkyl, C 16 alkyl, or C 7 alkyl. In certain embodiments wherein m is 2, R 2 is a C 8 branched chain alkyl group.
  • an agrochemical composition comprising. (i) an active ingredient, (ii) a surfactant, and (Hi) an aromatic ester of formula (I)
  • R 1 is di-Ci-Calkyl amino, hydroxyl, or halogen
  • q is an integer selected from 0 or 1
  • n is an integer selected from 0 to 20 inclusive
  • each A is independently C v 10 alkyl
  • m is an integer selected from 1 , 2 and 3; and wherein when m is 2 or 3, R 2 is Ci- C 20 alkyl; each group
  • each R ⁇ q, A and n is independently as defined above provided that the compound of formula (I) is not dipropylene glycol dibenzoate, and when m is an integer selected from 1 , R 2 is H or C 7 -C 20 alkyl.
  • Certain compounds of formula (I) are available commercially and include for example, those described in Table 1 below which are given a trade name. Other compounds are novel, and form a separate aspect of the invention.
  • Trideceth-5 benzoate Alternatively, aromatic esters of formula (I) may be prepared using well know reactions. See reaction schemes 1 and 2 below.
  • An alcohol of formula (A) is reacted with an acid anhydride of formula (AA) to form a benzoic acid ester of formula (I) plus an acid of formula (AC).
  • R 1 and q are as defined hereinbefore, and R represents the group -[AO] trustee-R 2 wherein A, n and R 2 are as defined hereinbefore.
  • Alcohols of formula (A), acid chlorides of formula (AC) and acid anhydrides of formula (AA) are readily available or may be synthesised using standard methodology well known in the art.
  • the present invention is based on the unexpected finding that compounds of formula (I) are particularly good adjuvants in agrochemical formulations. Accordingly, in one aspect, the invention provides the use of an aromatic ester of formula (I) as described herein as a synergist in an agrochemical composition
  • Such adjuvants may be combined with an active ingredient, which is an agrochemical, in order to form an agrochemical composition.
  • the present invention extends to a method of making such an agrochemical composition, wherein said method comprises combining a compound of formula (I) with an agrochemically active ingredient, and optionally a surfactant.
  • agrochemical and term “agrochemically active ingredient” are used herein interchangeably, and they include herbicides, insecticides, nematicides, molluscicides, funcgicides, plant growth regulators, and safeners, preferably herbicides, insecticides, and funcgicides.
  • Suitable herbicides include bicyclopyrone, mesotrione, fomesafen, tralkoxydim, napropamide, amitraz, propanil, pyrimethanil, dicloran, tecnazene, toclofos methyl, flamprop , 2,4-D, MCPA, mecoprop, clodinafop-propargyl, cyhalof op-butyl, diclofop methyl, haloxyfop, quizalofop-P, indol-3-ylacetic acid, 1-naphthylacetic acid, isoxaben, tebutam, chlorthal dimethyl, benomyl, benfuresate, dicamba, dichlobenil, benazolin, triazoxide, fluazuron, teflubenzuron, phenmedipham, acetochlor, alachlor, metolachlor, pretilachlor, thenylchlor,
  • Suitable fungicides include isopyrazam, mandipropamid, azoxystrobin, trifloxystrobin, kresoxim methyl, famoxadone, metominostrobin and picoxystrobin, cyprodanil, carbendazim, thiabendazole, dimethomorph, vinclozolin, iprodione, dithiocarbamate, imazalil, prochloraz, fluquinconazole, epoxiconazole, flutriafol, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, hexaconazole, paclobutrazole, propiconazole, tebuconazole, triadimefon, trtiticonazole, fenpropimorph, tridemorph, fenpropidin, mancozeb, metiram, chlorothalonil
  • Suitable insecticides include thiamethoxam, imidacloprid, acetamiprid, clothianidin, dinotefuran, nitenpyram, fipronil, abamectin, emamectin, bendiocarb, carbaryl, fenoxycarb, isoprocarb, pirimicarb, propoxur, xylylcarb, asulam, chlorpropham, endosulfan, heptachlor, tebufenozide, bensultap, diethofencarb, pirimiphos methyl, aldicarb, methomyl, cyprmethrin, bioallethrin, deltamethrin, lambda cyhalothrin, cyhalothrin, cyfluthrin, fenvalerate, imiprothrin, permethrin and halfenprox.
  • Suitable plant growth regulators include paclobutrazole and 1- methylcyclopropene.
  • Suitable safeners include benoxacor, cloquintocet-mexyl, cyometrinil, dichlormid, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, mefenpyr-diethyl, MG-191, naphthalic anhydride, and oxabetrinil.
  • Preferred agrochemical active ingredients are isopyrazam, epoxyconazole, fomesafen, mesotrione, pinoxaden, abamectin and nicosulfuron.
  • compositions of the invention may comprise one or more of the agrochemicals as described above.
  • compositions of the invention will typically comprise the agrochemical in an amount that is recommended in the art. Generally the agrochemical will be present at a concentration of about 0.001% to 90% w/w. The skilled man will appreciate that compositions of the invention may be in the form of a ready-to-use formulation or in concentrate form suitable for further dilution by the end user, and the concentration of agrochemical and compound of formula (I) will be adjusted accordingly. In concentrated form, compositions of the invention typically comprise agrochemical at 5 to 75% w/w, more preferably 10 to 50% w/w agrochemical. Ready-to-use compositions of the invention will typically comprise from 0.0001% to 1% w/w, more preferably from 0.001% to 0.5% w/w, and more preferably still from 0.001% to 0.1% w/w agrochemical.
  • compositions of the invention typically comprise a compound of formula (I) from 1% to 80% w/w, preferably from 5% to 60% w/w and more preferably from 10% w/w to 40% w/w.
  • Ready to use compositions of the invention typically comprise a compound of formula (I) from about 0.05% to about 1% w/w of the total composition, more preferably still from about 0.1% to about 0.5% w/w of the total composition.
  • the aromatic ester will be included at concentrations of 0.1%, 0.2%, 0.25%, 0.3%, 0.4% or 0.5% w/w of the total composition.
  • Compounds of formula (I) may be manufactured and/or formulated separately, and in order to be used as an adjuvant these may be added to a separate agrochemical formulation at a subsequent stage, typically immediately prior to use.
  • compositions of the invention may be formulated in any suitable manner known to the man skilled in the art.
  • a composition of the invention is a formulation concentrate which may be diluted or dispersed (typically in water) by an end-user (typically a farmer) in a spray tank prior to application.
  • Additional formulation components may be incorporated alongside compounds of formula (I) or compositions of the invention in such formulations.
  • additional components include, for example, adjuvants, surfactants, emulsifiers, and solvents, and are well known to the man skilled in the art: standard formulation publications disclose such formulation components suitable for use with the present invention (for example, Chemistry and Technology of Agrochemical Formulations, Ed. Alan Knowles, published by Kluwer Academic Publishers, The Netherlands in 1998; and Adjuvants and Additives: 2006 Edition by Alan Knowles, Agrow Report DS256, published by Informa UK Ltd, December 2006). Further standard formulation components suitable for use with the present invention are disclosed in WO2009/13028 A1 (see from page 46, line 5 to page 51 , line 40).
  • compositions of the present invention may also comprise one or more surfactants or dispersing agents to assist the emulsification of the agrochemical on dispersion or dilution in an aqueous medium (dispersant system).
  • the emulsification system is present primarily to assist in maintaining the emulsified agrochemical in water.
  • Many individual emulsifiers, surfactants and mixtures thereof suitable for forming an emulsion system for an agrochemical are known to those skilled in the art and a very wide range of choices is available.
  • Typical surfactants that may be used to form an emulsifier system include those containing ethylene oxide, propylene oxide or ethylene oxide and propylene oxide; aryl or alkylaryl sulphonates and combinations of these with either ethylene oxide or propylene oxide or both; carboxylates and combinations of these with either ethylene oxide or propylene oxide or both. Polymers and copolymers are also commonly used.
  • Compositions of the present invention may also include solvents, which may have a range of water solubilitites. Oils with very low water solubilities may be added to the solvent of the present invention for assorted reasons such as the provision of scent, safening, cost reduction, improvement of the emulsification properties and alteration of the solubilising power. Solvents with higher water solubility may also be added for various reasons, for instance to alter the ease with which the formulation emulsifies in water, to improve the solubility of the pesticide or of the other optional additives in the formulation, to change the viscosity of the formulation or to add a commercial benefit.
  • compositions which may be added to the formulation include for example, colourants, scents, and other materials which benefit a typical agrochemical formulation.
  • compositions of the invention may be formulated for example, as emulsion or dispersion concentrates, emulsions in water or oil, as a suspension of particles in an emulsion or oil, as microencapsulated formulations, aerosol sprays or fogging formulations; and these may be further formulated into granular materials or powders, for example for dry application or as water-dispersible formulations.
  • compositions of the invention will be formulated as, or comprised by an emulsion concentrate (EC), an emulsion in water (EW), a microcapsule formulation (CS), a suspension of particles with an emulsion of oil (suspoemulsion; SE), a dispersion concentrate (DC) or an oil suspension (OD).
  • compositions of the invention may be used to control pests.
  • pests includes insects, fungi, molluscs, nematodes, and unwanted plants.
  • a composition of the invention may be applied directly to the pest, or to the locus of a pest.
  • compositions of the invention also have utility in the seed treatment arena, and thus may be applied as appropriate to seeds.
  • Example 1 Use of benzoic acid ester adjuvants in agrochemical compositions comprising isopyrazam
  • Wheat plants were inoculated with the fungus Septoria tritici. Four days after inoculation the plants were sprayed with a diluted emulsion concentrate or suspension concentrate formulation of the fungicide isopyrazam at rates of 3, 10, 30 and 100 mg of the fungicide per litre of spray solution, using a laboratory track sprayer which delivered the spray at a rate of 200 litres per hectare. Spray tests were also carried out with diluted suspension concentrate additionally comprising each of the benzoate adjuvants described above. These adjuvants were added to the spray solution at a rate of 0.2 % w/w, based on the quantity of spray liquor. The leaves of the plants were assessed visually 1 days after the spray application and the damage was expressed as the percentage of the leaf area infected. Each spray test was replicated three times across the four application rates and the modelled means of these results are shown in Table 2 below.
  • compositions that were better at controlling S tritici than the standard isopyrazam emulsion concentrate formulation (Standard EC).
  • Table 2 Mean % infection of wheat plants with S. tritici treated with isopyrazam in the presence and absence of benzoic acid ester adjuvants. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Wheat plants were inoculated with the fungus Septoria tritici. Four days after inoculation the plants were sprayed with a diluted suspension concentrate formulation of the fungicide epoxyconazole at rates of 3, 10, 30 and 100 mg of the fungicide per litre of spray solution, using a laboratory track sprayer which delivered the spray at a rate of 200 litres per hectare. Spray tests were also carried out with diluted suspension concentrate additionally comprising each of the benzoate adjuvants described above. These adjuvants were added to the spray solution at a rate of 0.2 % w/w, based on the quantity of spray liquor. The leaves of the plants were assessed visually 1 days after the spray application and the damage was expressed as the percentage of the leaf area infected. Each spray test was replicated three times across the four application rates and the modelled means of these results are shown in Table 3 below.
  • Table 3 Mean % infection of wheat plants with S. tritici treated with epoxyconazole in the presence and absence of benzoic acid ester adjuvants. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Table 4 Mean % infection of wheat plants with S. tritici treated with isopyrazam in the presence and absence of 2-ethylhexyl 4-dimethylaminobenzoate. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • 2-ethylhexyl 4-dimethylaminobenzoate in compositions of isopyrazam resulted in a reduction S. tritici infection in comparison to treatment with the standard SC alone.
  • 2-ethylhexyl 4-dimethylaminobenzoate is an effective adjuvant for isopyrazam and such compositions are similar in efficacy to the standard EC isopyrazam formulation.
  • Example 5 Use of a C 12 -C 15 alkyl benzoate as an adjuvant for agrochemical
  • compositions comprising nicosulfuron
  • the aromatic ester Finsolv® TN (C 12 -C 15 alkyl benzoate) was tested in a glasshouse against four weed species using the herbicide nicosulfuron.
  • agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer, and was applied at a volume of 200 litres per hectare. Nicosulfuron was applied at either 30 or 60 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Abutilon theophrasti (ABUTH; growth stage 13), Chenopodium album (CHEAL; growth stage 1 ), Digitaria sanguineus (DIGSA; growth stage 13), and Setaria viridis (SETVI; growth stage 13).
  • Table 7 The results shown in Table 7 below are mean averages over the two rates of nicosulfuron, three replicates and the two assessment timings, and are compared to the efficacy of nicosulfuron in the absence of an adjuvant, and nicosulfuron in the presence of the commercially available tank-mix adjuvant, Atplus411F®.
  • Table 6 Mean percentage kill results for nicolsulfuron in the presence and absence of FinsolvDTN and Atplus 411 F®. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Table 7 Mean percentage kill results for nicolsulfuron in the presence and absence of FinsolvOTN and Atplus 411F®. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Ci 2 -C 15 benzoate is an effective adjuvant (with comparable efficacy to the commercially available tank-mix adjuvant Atplus411F®) for nicosulfuron.
  • Example 6 Use of a C 12 -C 15 alkyl benzoate as an aduvant for agrochemical
  • compositions comprising fomesafen
  • the aromatic ester Finsolv®TN (C 12 -C 15 alkyl benzoate) was tested in a glasshouse against four weed species using the herbicide fomesafen.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • Fomesafen was applied at either 60 or 120 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Chenopodium album (CHEAL;growth stage 14), Abutilon theophrasti (ABUTH; growth stage 12), Setaria viridis (SETVI; growth stage 13), and Xanthium strumarium (XANST; growth stage 12).
  • Example 7 Use of a C 2 -C 15 alkyl benzoate as an aduvant for agrochemical compositions comprising mesotrione
  • the aromatic ester Finsolv ®TN (C 12 -Ci 5 alkyl benzoate) was tested in a glasshouse against three weed species using the herbicide mesotrione.
  • agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • Mesotrione was applied at either 60 or 120 grams of pesticide per hectare on weeds which had been grown to the 1.3 or 1.4 leaf stage.
  • the weed species were Xanthium strumarium (XANST), Brachiaria platyphylla (BRAPL), and Digitaria sanguinalis (DIGSA).
  • XANST Xanthium strumarium
  • BRAPL Brachiaria platyphylla
  • DIGSA Digitaria sanguinalis
  • Tetronic® 1107 was used in the spray tank at a concentration of 0.036 g/l alongside the lower concentration of mesotrione and at a concentration of 0.072 g/l at the higher concentration of mesotrione.
  • Table 11 The results shown in Table 11 below are mean averages over the two rates of mesotrione, three replicates, the three assessment timings, and the three weed species, and are compared to the efficacy of mesotrione in the absence of adjuvant and mesotrione in the presence of the well-known adjuvant Tween® 20.
  • Table 11 Mean percentage kill results for mesotrione in the presence and absence of Finsolv® TN or Tween® 20.
  • a standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different
  • compositions comprising pinoxaden
  • the aromatic ester Finsolv®TN (C 12 -C15 alkyl benzoate) was tested in a glasshouse against four weed species using the herbicide pinoxaden.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • Pinoxaden was applied at either 7.5 or 15 grams of pesticide per hectare on each of the weed species.
  • the commercially available surfactant Atlas® G5000 was used in the spray tank at a concentration of 0.00375 g/l alongside the lower concentration of pinoxaden and at a concentration of 0.0075 g/l at the higher concentration of pinoxaden.
  • Alopecurus myosuroides Alopecurus myosuroides
  • Avena fatua Avena fatua
  • LLOLPE Lolium perenne
  • Setaria viridis Setaria viridis
  • Table 12 Mean percentage kill results for pinoxaden in the presence and absence of Finsolv®TN or Tween®20.
  • the adjuvant mixture "Benzoate 1" was synthesised by adding an oil comprising a mixture of linear long chain (16 and 17 carbons in length) alcohols to a flask and reacting this oil with benzoyl chloride. The resulting mixture was extracted after the reaction and purified. Analysis by nmr showed that the product consisted of long-chain (16 and 17 carbons in length) benzoates. This benzoic acid ester was tested as an adjuvant in Examples 0, 1 1 , 12, and 13 described supra.
  • Example 10 Use of benzoic acid ester adjuvants in agrochemical compositions comprising nicosulfuron
  • the aromatic esters Benzoate 1 (see Example 9), Benzoflex 354 (2,2,4- trimethyl-1 ,3-pentanediol dibenzoate) and Finsolv®SB (stearyl benzoate) were tested in a glasshouse against four weed species using the herbicide nicosulfuron. Nicosulfuron was applied at either 30 or 60 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Abutilon theophrasti (ABUTH; growth stage 13), Chenopodium albu (CHEAL; growth stage 14), Digitaria sanguinalis (DIGSA; growth stage 13), and Setaria viridis (SETVI; growth stage 13). Each spray test replicated three times.
  • the efficacy of the herbicide was assessed visually and expressed as a percentage of the leaf area killed. Samples were assessed at time periods of 14 and 20 days following application. The results shown in Table 14 below are mean averages over the two rates of nicosulfuron, three replicates and the two assessment timings, and are compared to the efficacy of nicosulfuron in the absence of an adjuvant, and nicosulfuron in the presence of the commercially available tank-mix adjuvant, Atplus41 1 F®.
  • Example 11 Use of benzoic acid ester adjuvants in agrochemical compositions comprising fomesafen
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare. Fomesafen was applied at either 60 or 120 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Chenopodium album (CHEAL;growth stage 14), Abutilon theophrasti (ABUTH; growth stage 12), Setaria viridis (SETVI; growth stage 13), and Xanthium strumarium (XANST; growth stage 12).
  • Table 15 Mean percentage kill results for fomesafen in the presence and absence of benzoate 1 , benzoflex 354, Finsolv ®S8 or Turbocharge®. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Example 12 Use of benzoic acid ester adjuvants in agrochemical compositions comprising mesotrione
  • the aromatic esters benzoate 1 (see Example 9), Benzoflex 354 (2,2,4-trimethyl- 1 ,3-pentanediol dibenzoate) and Finsolv®SB (stearyl benzoate) were tested in a glasshouse against three weed species using the herbicide mesotrione.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • Mesotrione was applied at either 60 or 120 grams of pesticide per hectare on weeds which had been grown to the 1.3 or 1.4 leaf stage.
  • the weed species were Xanthium strumarium (XANST), Brachiaria platyphylla (BFtAPL), and Digitaria sanguinalis (DIGSA).
  • the commercially available surfactant Tetronic® 1107 was used in the spray tank at a concentration of 0.036 g/l alongside the lower concentration of mesotrione and at a concentration of 0.072 g/l at the higher concentration of mesotrione.
  • Benzoflex 354, Finsolv®SB (stearyl benzoate) or Brij ®96 A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Example 13 Use of benzoic acid ester adjuvants in agrochemical compositions comprising pinoxaden
  • the aromatic esters benzoate 1 (see Example 9), Benzoflex 354 (2,2,4-trimethyt- 1 ,3-pentanediol dibenzoate) and Finsolv®SB (stearyl benzoate) were tested in a glasshouse against four weed species using the herbicide pinoxaden.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare. Pinoxaden was applied at either 7.5 or 15 grams of pesticide per hectare on each of the weed species.
  • the commercially available surfactant Atlas® G5000 was used in the spray tank at a concentration of 0.00375 g/l alongside the lower concentration of pinoxaden and at a concentration of 0.0075 g/l at the higher concentration of pinoxaden.
  • the weed species and their growth stage at spraying were Alopecurus myosuroides (ALOMY; growth stage 13), Avena fatua (AVEFA; growth stage 12); Lolium perenne (LOLPE; growth stage 13), Setaria viridis (SETVI; growth stage 14).
  • Alopecurus myosuroides Alopecurus myosuroides
  • AVEFA Avena fatua
  • LPE Lolium perenne
  • SETVI Setaria viridis
  • Table 17 The results shown in Table 17 below are mean averages over the two rates of pinoxaden, three replicates and the three assessment timings, and are compared to the efficacy of pinoxaden in the absence of an adjuvant and pinoxaden in the presence ofBrij®96 .
  • Benzoflex 354, FinsolvOSB (stearyl benzoate) or Brij ®96 A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Example 1 Use of benzoic acid ester adjuvants in agrochemical compositions comprising pinoxaden
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • the adjuvant oils were emulsified using a small amount of the surfactant Pluronic® PE 10500, which was present in the composition at a concentration of 0.02 % v/v.
  • Pinoxaden was applied at either 7.5 or 15 grams of pesticide per hectare on each of the weed species.
  • the commercially available surfactant Atlas® G5000 was used in the spray tank at a concentration of 0.00375 g/l alongside the lower concentration of pinoxaden and at a concentration of 0.0075 g/l at the higher concentration of pinoxaden.
  • the weed species and their growth stage at spraying were Alopecurus myosuroides (ALOMY; growth stage 13), Avena fatua (AVEFA; growth stage 12); Lolium perenne (LOLPE; growth stage 13), Setaria viridis (SETVI; growth stage 13-14). Each spray test was replicated three times. The efficacy of the herbicide was assessed visually and expressed as a percentage of the leaf area killed. Samples were assessed at time periods of 14 and 21 days following application.
  • Table 18 The results shown in Table 18 below are mean averages over the two rates of pinoxaden, three replicates and the two assessment timings, and are compared to the efficacy of pinoxaden in the absence of an adjuvant and pinoxaden in the presence of tris 2ethylhexylphosphate (TEHP) .
  • TEHP tris 2ethylhexylphosphate
  • Example 15 Use of benzoic acid ester adjuvants in agrochemical compositions comprising nicosulfuron
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • the adjuvant oils were emulsified using a small amount of the surfactant Pluronic® PE 10500, which was present in the composition at a concentration of 0.02 % v/v. Nicosulfuron was applied at either 30 or 60 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Abutiion theophrasti (ABUTH; growth stage 13), Chenopodium album (CHEAL; growth stage 14-15), Digitaria sanguineus (DIGSA; growth stage 14), and Setaria viridis (SETVI; growth stage 13-14).
  • Example 16 Use of benzoic acid ester adjuvants in agrochemical compositions comprising fomesafen
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • the adjuvant oils were emulsified using a small amount of the surfactant Pluronic® PE 10500, which was present in the composition at a concentration of 0.02 % v/v.
  • Fomesafen was applied at either 60 or 120 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Polygonum convolvulus (POLCO;growth stage 13-14), Brachiaria plantaginea (BRAL; growth stage 13-14), Digitaria sanguinalis (DIGSA; growth stage 14), and Commelina benghalensis (COMBE; growth stage 13-14).
  • POLCO Polygonum convolvulus
  • BRAL Brachiaria plantaginea
  • DIGSA Digitaria sanguinalis
  • COMBE Commelina benghalensis
  • Example 17 Use of benzoic acid ester adjuvants in agrochemical compositions comprising mesotrione
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • the adjuvant oils were emulsified using a small amount of the surfactant Pluronic® PE 10500, which was present in the composition at a concentration of 0.02 % v/v.
  • Mesotrione was applied at either 60 or 120 grams of pesticide per hectare on weeds which had been grown to the 1.3 or 1.4 leaf stage.
  • the weed species were Xanthium strutnarium (XANST), Brachiaria platyphylla (BRAPL), and Digitaria sanguineus (DIGSA).
  • the commercially available surfactant Tetronic® 1 107 was used in the spray tank at a concentration of 0.036 g/l alongside the lower concentration of mesotrione and at a concentration of 0.072 g/l at the higher concentration of mesotrione. Each spray test was replicated three times. The efficacy of the herbicide was assessed visually and expressed as a percentage of the leaf area killed. Samples were assessed at time periods of 14 and 21 days following application. The results shown in Table 10 below are mean averages over the two rates of mesotrione, three replicates and the two assessment timings, and are compared to the efficacy of mesotrione in the absence of adjuvant and mesotrione in the presence of the well-known adjuvant Tween®20.
  • results shown in Table 16 below are mean averages over the two rates of mesotrione, three replicates, three assessment timings and three weed species. The results are compared to the efficacy of mesotrione in the absence of an adjuvant and mesotrione in the presence of the commercially available adjuvant Tween®20.
  • Example 18 Use of benzoic acid ester adjuvants in agrochemical compositions comprising pinoxaden
  • the aromatic esters Finsolv®TN and the aromatic ester ethoxylate Dermol 25-3B were tested in a glasshouse against four weed species using the herbicide pinoxaden.
  • An agrochemical composition was prepared containing either 0.2, 0.1 , 0.05 or 0.025 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • the adjuvant tris(2-ethylhexyl) phosphate was applied at 0.5 % v/v.An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • Pinoxaden was applied at either 7.5 or 15 grams of pesticide per hectare on each of the weed species.
  • the commercially available surfactant Atlas® G5000 was used in the spray tank at a concentration of 0.00375 g/l alongside the lower concentration of pinoxaden and at a concentration of 0.0075 g/l at the higher concentration of pinoxaden.
  • Alopecurus myosuroides Alopecurus myosuroides
  • Avena fatua Avena fatua
  • LPE Lolium perenne
  • Setaria viridis SETVI; growth stage 12
  • Example 19 Use of benzoic acid ester adjuvants in agrochemical compositions comprising nicosulfuron
  • the aromatic ester Finsolv®TN and the aromatic ester ethoxylate Dermol® 25- 3B were tested in a glasshouse against four weed species using the herbicide nicosulfuron.
  • An agrochemical composition was prepared containing either 0.2, 0.1 , 0.05 or 0.025 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • the commercial adjuvant Atplus ®411F was applied at 0.5 % v/v. Nicosulfuron was applied at either 30 or 60 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Abutilon theophrasti (ABUTH; growth stage 1 1-12), Chenopod/um album (CHEAL; growth stage 13-15), Digiiaria sanguineus (DIGSA; growth stage 3-21), and Sefan ' a viridis (SETVI; growth stage 13).
  • ABUTH Abutilon theophrasti
  • CHEAL Chenopod/um album
  • DIGSA Digiiaria sanguineus
  • SETVI Sefan ' a viridis
  • Example 20 Use of benzoic acid ester adjuvants in agrochemica) compositions comprising fomesafen
  • An agrochemical composition was prepared containing either 0.2, 0.1 , 0.05 or 0.025 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • the commercial adjuvant Turbocharge ® was applied at 0.5 % v/v.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • Fomesafen was applied at either 60 or 120 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Polygonum convolvulus
  • Table 24 Mean percentage kilt results for fomesafen In the presence and absence of Finsolv®TN and the aromatic ester ethoxylate Dermol 25-3B or Turbocharge®. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Fomesafen 17.8E The results demonstrate that all of the benzoic acid esters tested are effective as adjuvants for fomesafen and that Finsolv SB and Dermol 25-3B are as effective as the commercially available agrochemical adjuvant Turbocharge® but at a much lower use rate of the adjuvant.
  • Example 21 Use of benzoic acid ester adjuvants in agrochemical compositions comprising mesotrione
  • An agrochemical composition was prepared containing either 0.2, 0.1 , 0.05 or 0.025 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • the commercial adjuvant Tween20 ® was applied at 0.2 % v/v.
  • Mesotrione was applied at either 60 or 120 grams of pesticide per hectare on weeds which had been grown to the 1.3 or 1.4 leaf stage.
  • Tetronic® 1107 was used in the spray tank at a concentration of 0.036 gll alongside the lower concentration of mesotrione and at a concentration of 0.072 g/l at the higher concentration of mesotrione.
  • the weed species were Polygonum convolvulus (POLCO) 13, Brachiaria platyphylla (BRAPL) 12-13, Comelina berghalensis (COMBE) 12 and Digitaria sanguinalis (DIGSA) 13.
  • Table 25 Mean percentage kill results for mesotrione in the presence and absence of Finsolv®TN and the aromatic ester ethoxylate Dermol ®25-3B orTween®20.
  • a standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • the novel compounds oleyl-2- ethoxy-benzoate and oleyl-10- ethoxy-benzoate are synthesised.
  • the adjuvant mixture "Benzoate 2" was synthesised by adding an ethoxylated surfactant (Brij ®0-2) comprising a mixture of linear long chain (primarily oley!, 18 carbons in length) alcohols to a flask and reacting this oil with benzoyl chloride. The resulting mixture was extracted after the reaction and purified. Analysis by nmr showed that the product consisted of long-chain (18 carbons in length) alcohol ethoxylates with a terminal benzoate. Similarly the surfactant Brij ®O-10 was reacted with benzoyl chloride to form the benzoate "Benzoate 3". These benzoic acid esters were tested as adjuvants in Examples 23, 24, 25, and 26 described infra.
  • Example 23 Use of benzoic acid ester adjuvants in agrochemical compositions comprising pinoxaden
  • the two aromatic esters prepared in example 22 tested in a glasshouse against four weed species using the herbicide pinoxaden.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare. Pinoxaden was applied at either 7.5 or 15 grams of pesticide per hectare on each of the weed species.
  • the commercially available surfactant Atlas® G5000 was used in the spray tank at a concentration of 0.00375 g/l alongside the lower concentration of pinoxaden and at a concentration of 0.0075 g/l at the higher concentration of pinoxaden.
  • the weed species and their growth stage at spraying were Alopecurus myosuroides (ALOMY; growth stage 13), A vena fatua (AVEFA; growth stage 12); Loliu perenne (LOLPE; growth stage 13), Setaria viridis (SETVI; growth stage 13-14).
  • the two aromatic esters prepared in example 22 tested in a glasshouse against four weed species using the herbicide nicosulfuron. Nicosulfuron was applied at either 30 or 60 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Abutilon theophrasti (ABUTH; growth stage 13), Chenopodium album (CHEAL; growth stage 14-15), Digitaria sanguinalis (DIGSA; growth stage 14), and Setaria viridis (SETVI; growth stage 13-14). Each spray test replicated three times.
  • the efficacy of the herbicide was assessed visually and expressed as a percentage of the leaf area killed. Samples were assessed at time periods of 14 and 21 days following application.
  • Table 27 The results shown in Table 27 below are mean averages over the two rates of nicosulfuron, three replicates and the two assessment timings, and are compared to the efficacy of nicosulfuron in the absence of an adjuvant, and nicosulfuron in the presence of the commercially available tank-mix adjuvant, Atplus41 1 F®.
  • Table 27 Mean percentage kill results for nicosulfuron in the presence and absence of Benzoate 2 and Benzoate 3.
  • a standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Example 25 Use of benzoic acid ester adjuvants in agrochemical compositions comprising fomesafen
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare. Fomesafen was applied at either 60 or 120 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Polygonum convolvulus (POLCO;growth stage 13), Brachiaria plantaginea (BRAL; growth stage 13), Digitaria sanguinalis (DIGSA; growth stage 12-13), and Commelina benghalensis
  • Example 26 Use of benzoic acid ester adjuvants in agrochemical compositions comprising mesotrione
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • Mesotrione was applied at either 60 or 120 grams of pesticide per hectare on weeds which had been grown to the 1.3 or 1.4 leaf stage.
  • the commercially available surfactant Tetronic® 1107 was used in the spray tank at a concentration of 0.036 g/l alongside the lower concentration of mesotrione and at a concentration of 0.072 g/l at the higher
  • weed species were Xanthium strumarium (XA ST), Brachiaria platyphylla (BFIAPL), and Digitaria sanguina!is (DIGSA).
  • Example 27 A further example of a novel benzoate capped ethoxylated adjuvant
  • Example 28 Use of benzoic acid ester adjuvants in agrochemical compositions comprising isopyrazam
  • Wheat plants were inoculated with the fungus Septoria tritici. Four days after inoculation the plants were sprayed with a diluted emulsion concentrate or suspension concentrate formulation of the fungicide isopyrazam at rates of 3, 10, 30 and 100 mg of the fungicide per litre of spray solution, using a laboratory track sprayer which delivered the spray at a rate of 200 litres per hectare. Spray tests were also carried out with diluted suspension concentrate additionally comprising each of the benzoate adjuvants described above. These adjuvants were added to the spray solution at a rate of 0.2 % w/w, based on the quantity of spray liquor. The leaves of the plants were assessed visually 14 days after the spray application and the damage was expressed as the percentage of the leaf area infected. Each spray test was replicated three times across the four application rates and the modelled means of these results are shown in Table 30 below.
  • Table 30 Mean % infection of wheat plants with S. tritici treated with isopyrazam in the presence and absence of benzoic acid ester adjuvants. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Example 29 Use of benzoic acid ester adjuvants in agrochemical compositions comprising epoxyconazole
  • Wheat plants were inoculated with the fungus Septoria tritici. Four days after inoculation the plants were sprayed with a diluted suspension concentrate formulation of the fungicide epoxyconazole at rates of 3, 10, 30 and 100 mg of the fungicide per litre of spray solution, using a laboratory track sprayer which delivered the spray at a rate of 200 litres per hectare. Spray tests were also carried out with diluted suspension concentrate additionally comprising each of the benzoate adjuvants described above. These adjuvants were added to the spray solution at a rate of 0.2 % w/w, based on the quantity of spray liquor. The leaves of the plants were assessed visually 14 days after the spray application and the damage was expressed as the percentage of the leaf area infected. Each spray test was replicated three times across the four application rates and the modelled means of these results are shown in Table 31 below.
  • Table 31 Mean % infection of wheat plants with S. tritici treated with epoxyconazole in the presence and absence of benzoic acid ester adjuvants. A standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Sunspray 11N is a commercially available oil which can be used to formulate adjuvants for tank mixing with agrochemical peroducts.
  • One of the problems with ethoxylated adjuvants is that they are often incompatible with such oils and cannot therefore be formulated with this oil. This is a limitation.
  • An advantage of a benzoate ester end capped adjuvant is that it has excellent compatibility with oils such as Sunspray 11N.
  • the Agnique FOH OC9 10B formed two distinct layers whereas the benzoate end cap formed a single layer. This demonstrates the superior miscibility of benzoate end capped adjuvants to butyl end capped adjuvants.
  • Example 31 Further benzoate end capped ethoxylated surfactants
  • Example 32 Use of benzoic acid ester adjuvants in agrochemical compositions comprising pinoxaden
  • the aromatic compound tridecyl salicylate was tested in a glasshouse against four weed species using the herbicide pinoxaden.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare. Pinoxaden was applied at either 7.5 or 15 grams of pesticide per hectare on each of the weed species.
  • the commercially available surfactant Atlas® G5000 was used in the spray tank at a concentration of 0.00375 g/l alongside the lower concentration of pinoxaden and at a concentration of 0.0075 g/l at the higher concentration of pinoxaden.
  • Alopecurus myosuroides Alopecurus myosuroides
  • Avena fatua Avena fatua
  • LLOLPE Loltum perenne
  • Setaria viridis SETVI; growth stage 13-14.
  • Table 32 Mean percentage kill results for pinoxaden in the presence and absence of tridecyl salicylate or TEHP.
  • a standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Example 33 Use of benzoic acid ester adjuvants in agrochemical compositions comprising nicosulfuron
  • the aromatic compound tridecyl salicylate was tested in a glasshouse against four weed species using the herbicide nicosulfuron. Nicosulfuron was applied at either 30 or 60 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Abutilon theophrasti (ABUTH; growth stage 13), Chenopodium album (CHEAL; growth stage 14-15), Digitaria sanguinalis (DIGSA; growth stage 14), and Setaria viridis (SETVI; growth stage 13-14).
  • Example 34 Use of benzoic acid ester adjuvants in agrochemical compositions comprising fomesafen
  • the aromatic compound tridecyl salicylate was tested in a glasshouse against four weed species using the herbicide fomesafen.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare. Fomesafen was applied at either 60 or 120 grams of pesticide per hectare on each of the weed species.
  • the weed species and their growth stage at spraying were Polygonum convolvulus (POLCO;growth stage 13-14), Brachiaria plantaginea (BRAL; growth stage 13-14), Digitaria sanguineus (DIGSA; growth stage 14), and Commelina benghalensis (COMBE; growth stage 13-14).
  • Example 35 Use of benzoic acid ester adjuvants in agrochemical compositions comprising mesotrione
  • the aromatic compound tridecyl salicylate was tested in a glasshouse against three weed species using the herbicide mesotrione.
  • An agrochemical composition was prepared containing 0.2 % v/v of the adjuvant in a track sprayer and was applied at a volume of 200 litres per hectare.
  • Mesotrione was applied at either 60 or 120 grams of pesticide per hectare on weeds which had been grown to the 1.3 or 1.4 leaf stage.
  • the commercially available surfactant Tetronic® 1107 was used in the spray tank at a concentration of 0.036 g/l alongside the lower concentration of mesotrione and at a concentration of 0.072 g/l at the higher concentration of mesotrione.
  • the weed species were Xanthium strumarium (XANST), Brachiaria platyphylla (BRAPL), and Digitaria sanguinalis (DIGSA).
  • results are compared to the efficacy of mesotrione in the absence of an adjuvant and mesotrione in the presence of the commercially available adjuvant Tween®20.
  • a standard Tukey HSD test was carried out to assess whether each result was statistically different from the other results and this is expressed as a letter: tests with the same letter are not statistically different (p ⁇ 0.05).
  • Finsolv®TN (Ci 2 -C 15 alkyl benzoate) and the aromatic ester ethoxylate Dermol®25-3B (C 12 -Ci5 alkyl ethoxy (3) benzoate) as adjuvants in compositions containing abamectin was tested and compared to the efficacy of abamectin compositions which lack this type of adjuvant.
  • the adjuvants were present at 0.1 % v/v in the abamectin compositions.
  • the surfactants polyoxyethylene sorbitan monooleate and an ethoxylated castor oil were also present in all the abamectin compositions tested.
  • Two week old French bean (Phaseolus vulgaris) plants were infested with a mixed population of two spotted spider mite Tetranychus urticae.
  • One day after infestation the plants were treated with the test compositions, with a track sprayer from the top with a rate of 200 litres per hectare. Plants were incubated in the greenhouse for 10 days and the evaluation was done on mortality against Larva and Adults, just on the lower side (untreated) of the leaves. Each experiment was replicated twice and the results were averaged. The mortality against Larva and Adults was then averaged.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Cette invention porte sur l'utilisation d'esters aromatiques comme adjuvants dans des compositions, en particulier destinées à un usage agrochimique, ainsi que sur des compositions comprenant un tel ester aromatique, en association avec au moins un agent agrochimique et au moins un tensioactif. L'invention porte en outre sur des procédés de fabrication et d'utilisation de telles compositions. En particulier, la présente invention porte sur de telles compositions lorsqu'elles sont formulées sous forme d'un concentré émulsionnable (EC), d'une émulsion dans de l'eau (EW), de suspension de particules dans de l'eau (SC), d'une formulation de microcapsules (CS), d'une suspension de particules avec une émulsion (SE), d'un concentré de dispersion (DC) ou d'une suspension huileuse (OD), ou lorsqu'elles comprennent ceux-ci.
PCT/GB2012/000341 2011-04-26 2012-04-13 Composant de formulation WO2012146889A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US14/113,678 US10206388B2 (en) 2011-04-26 2012-04-13 Formulation component
CN201280020196.XA CN103491786B (zh) 2011-04-26 2012-04-13 配制品组分
BR112013027279A BR112013027279B8 (pt) 2011-04-26 2012-04-13 composição concentrada de formulação agroquímica adequada para diluição adicional; utilização de um éster aromático e método de controle de uma praga, bem como método de fabricação de uma composição concentrada de formulação agroquímica adequada para diluição adicional
EP12716512.4A EP2701518B1 (fr) 2011-04-26 2012-04-13 Composant de formulation
ES12716512T ES2711639T3 (es) 2011-04-26 2012-04-13 Componente de formulación

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB1107039.8A GB201107039D0 (en) 2011-04-26 2011-04-26 Formulation component
GB1107039.8 2011-04-26

Publications (2)

Publication Number Publication Date
WO2012146889A1 true WO2012146889A1 (fr) 2012-11-01
WO2012146889A4 WO2012146889A4 (fr) 2013-01-03

Family

ID=44168615

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2012/000341 WO2012146889A1 (fr) 2011-04-26 2012-04-13 Composant de formulation

Country Status (10)

Country Link
US (1) US10206388B2 (fr)
EP (1) EP2701518B1 (fr)
CN (1) CN103491786B (fr)
AR (1) AR086183A1 (fr)
BR (1) BR112013027279B8 (fr)
ES (1) ES2711639T3 (fr)
GB (1) GB201107039D0 (fr)
TW (2) TWI684409B (fr)
UY (1) UY34031A (fr)
WO (1) WO2012146889A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014057064A2 (fr) * 2012-10-12 2014-04-17 Syngenta Limited Adjuvants

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2533083B (en) * 2014-12-02 2019-09-18 Rotam Agrochem Int Co Ltd An agrochemical composition, a method of preparing the same and the use thereof
EP3259323B1 (fr) 2015-02-20 2020-02-26 3M Innovative Properties Company Oligomères d'addition-fragmentation
CN111296464A (zh) * 2020-03-19 2020-06-19 利尔化学股份有限公司 一种含有唑啉草酯的除草组合物
AR128055A1 (es) 2022-12-21 2024-03-20 Surcos Impact Sarl Composición de clorotalonil en forma de suspoemulsión

Citations (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5059516A (fr) * 1973-10-03 1975-05-22
US4245030A (en) * 1979-05-23 1981-01-13 Hoechst Aktiengesellschaft Photopolymerizable mixture containing improved plasticizer
GB2181429A (en) * 1985-08-13 1987-04-23 Canon Kk Optically active lactic acid derivatives useful in liquid crystal compositions
US4791097A (en) * 1987-03-09 1988-12-13 Finetex, Inc. Benzoic acid esters and their use
JPH0350246A (ja) * 1989-07-17 1991-03-04 Kyowa Yuka Kk 新規可塑剤
JPH0350266A (ja) * 1989-07-17 1991-03-04 Dainippon Ink & Chem Inc ポリサルファイド重合体用縮合系可塑剤、ポリサルファイド重合体組成物及びシーリング材
JPH0359045A (ja) * 1989-07-28 1991-03-14 Dainippon Ink & Chem Inc ゴム用縮合系可塑剤及びゴム組成物
JPH05339413A (ja) * 1992-06-10 1993-12-21 Tosoh Corp 発泡成形用ポリ塩化ビニルプラスチゾル組成物および該組成物を用いたポリ塩化ビニル樹脂発泡体の製造方法
US5271930A (en) * 1991-11-20 1993-12-21 Finetex, Inc. Benzoate esters of polyalkoxylated block copolymers
WO1995017817A1 (fr) * 1993-12-28 1995-07-06 Kao Corporation Composition activatrice destinee aux produits chimiques agricoles et compositions de produits chimiques agricoles
JPH08127964A (ja) * 1994-10-31 1996-05-21 Sanyo Chem Ind Ltd 合成繊維用処理剤
US5626859A (en) * 1993-12-30 1997-05-06 Fitch; Joanne A. Ectoparasite control stick for domesticated animals
EP0974575A1 (fr) * 1997-02-28 2000-01-26 New Japan Chemical Co.,Ltd. Esters para-hydroxybenzoiques, plastifiant les contenant, composition a base de resine polyamidique et objets moules
WO2002009519A1 (fr) * 2000-07-20 2002-02-07 Cognis Iberia S. L. Utilisation d'esters quaternaires comme agents microbicides
JP2004059517A (ja) * 2002-07-30 2004-02-26 New Japan Chem Co Ltd ヒドロキシ安息香酸エステル類の製造方法
JP2004067756A (ja) * 2002-08-02 2004-03-04 Dainippon Ink & Chem Inc 樹脂組成物
EP1403322A1 (fr) * 2001-06-13 2004-03-31 Kao Corporation Plastifiant pour resine polyester
CN100338019C (zh) * 2006-06-28 2007-09-19 聊城大学 一种月桂醇聚氧乙烯醚苯甲酸酯及其合成方法
WO2009130281A1 (fr) 2008-04-24 2009-10-29 Basf Se Alcoxylates d'alcool, agents les contenant et utilisation desdits alcoxylates d'alcool comme adjuvants dans le domaine agrochimique
WO2010115721A2 (fr) * 2009-04-02 2010-10-14 Basf Se Procédé permettant de réduire les lésions dues aux brûlures solaires chez les plantes

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4560534A (en) 1983-11-02 1985-12-24 Miles Laboratories, Inc. Polymer catalyst transducers
JP3050246B2 (ja) 1990-08-23 2000-06-12 日本電気株式会社 ２線ファクシミリインターフェイス付オーダーワイヤ装置
JP3050266B2 (ja) 1993-10-20 2000-06-12 株式会社いすゞセラミックス研究所 セラミックス発熱体及びその製造方法
JP3059045B2 (ja) 1994-03-24 2000-07-04 株式会社東芝 画像形成記憶装置
EP1408748A1 (fr) * 2000-05-15 2004-04-21 Imperial Chemical Industries PLC Traitement de pulverisation agrochimique et preparations a pulveriser
EP1210877A1 (fr) * 2000-12-01 2002-06-05 Aventis CropScience GmbH Formulation de type émulsion huile-dans-eau pour insecticides
NO319194B1 (no) * 2002-11-14 2005-06-27 Pronova Biocare As Lipase-katalysert forestringsfremgangsmate av marine oljer
JP2009508908A (ja) * 2005-09-23 2009-03-05 ビーエーエスエフ ソシエタス・ヨーロピア 新規の農薬製剤
JP5339413B2 (ja) 2008-09-02 2013-11-13 株式会社大一商会 遊技機
WO2011015220A1 (fr) * 2009-08-07 2011-02-10 Gat Microencapsulation, Ag Microcapsules contenant les lactones macrolides abamectine, milbémectine, avermectines, milbémycines, émamectines, ivermectines et mectines en général

Patent Citations (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5059516A (fr) * 1973-10-03 1975-05-22
US4245030A (en) * 1979-05-23 1981-01-13 Hoechst Aktiengesellschaft Photopolymerizable mixture containing improved plasticizer
GB2181429A (en) * 1985-08-13 1987-04-23 Canon Kk Optically active lactic acid derivatives useful in liquid crystal compositions
US4791097A (en) * 1987-03-09 1988-12-13 Finetex, Inc. Benzoic acid esters and their use
JPH0350246A (ja) * 1989-07-17 1991-03-04 Kyowa Yuka Kk 新規可塑剤
JPH0350266A (ja) * 1989-07-17 1991-03-04 Dainippon Ink & Chem Inc ポリサルファイド重合体用縮合系可塑剤、ポリサルファイド重合体組成物及びシーリング材
JPH0359045A (ja) * 1989-07-28 1991-03-14 Dainippon Ink & Chem Inc ゴム用縮合系可塑剤及びゴム組成物
US5271930A (en) * 1991-11-20 1993-12-21 Finetex, Inc. Benzoate esters of polyalkoxylated block copolymers
JPH05339413A (ja) * 1992-06-10 1993-12-21 Tosoh Corp 発泡成形用ポリ塩化ビニルプラスチゾル組成物および該組成物を用いたポリ塩化ビニル樹脂発泡体の製造方法
WO1995017817A1 (fr) * 1993-12-28 1995-07-06 Kao Corporation Composition activatrice destinee aux produits chimiques agricoles et compositions de produits chimiques agricoles
US5626859A (en) * 1993-12-30 1997-05-06 Fitch; Joanne A. Ectoparasite control stick for domesticated animals
JPH08127964A (ja) * 1994-10-31 1996-05-21 Sanyo Chem Ind Ltd 合成繊維用処理剤
EP0974575A1 (fr) * 1997-02-28 2000-01-26 New Japan Chemical Co.,Ltd. Esters para-hydroxybenzoiques, plastifiant les contenant, composition a base de resine polyamidique et objets moules
WO2002009519A1 (fr) * 2000-07-20 2002-02-07 Cognis Iberia S. L. Utilisation d'esters quaternaires comme agents microbicides
EP1403322A1 (fr) * 2001-06-13 2004-03-31 Kao Corporation Plastifiant pour resine polyester
JP2004059517A (ja) * 2002-07-30 2004-02-26 New Japan Chem Co Ltd ヒドロキシ安息香酸エステル類の製造方法
JP2004067756A (ja) * 2002-08-02 2004-03-04 Dainippon Ink & Chem Inc 樹脂組成物
CN100338019C (zh) * 2006-06-28 2007-09-19 聊城大学 一种月桂醇聚氧乙烯醚苯甲酸酯及其合成方法
WO2009130281A1 (fr) 2008-04-24 2009-10-29 Basf Se Alcoxylates d'alcool, agents les contenant et utilisation desdits alcoxylates d'alcool comme adjuvants dans le domaine agrochimique
WO2010115721A2 (fr) * 2009-04-02 2010-10-14 Basf Se Procédé permettant de réduire les lésions dues aux brûlures solaires chez les plantes

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
"Agrow Report DS256", 2006, INFORMA UK LTD, article "Adjuvants and Additives"
"Chemistry and Technology of Agrochemical Formulations", 1998, KLUWER ACADEMIC PUBLISHERS
HESS, F.D.; FOY, C.L., WEED TECHNOLOGY, vol. 14, 2000, pages 807 - 813
INNOSPEC: "Finsolv TPP", INTERNET CITATION, 1 January 2008 (2008-01-01), XP007907237, Retrieved from the Internet <URL:http://www.innospecinc.com/assets/_files/documents/may_08/cm__1210344975_Finsolv_TPP.pdf> [retrieved on 20090216] *
K. STEINBECK ET AL: "Baseninduzierte ringöffnung von 1,3-dioxolanen: ein neuer weg zu dienolethern", TETRAHEDRON LETTERS, vol. 21, no. 16, 1 January 1980 (1980-01-01), pages 1515 - 1518, XP055032338, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)92761-8 *
See also references of EP2701518A1 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014057064A2 (fr) * 2012-10-12 2014-04-17 Syngenta Limited Adjuvants
WO2014057064A3 (fr) * 2012-10-12 2014-10-30 Syngenta Limited Adjuvants
US9456599B2 (en) 2012-10-12 2016-10-04 Syngenta Limited Adjuvants

Also Published As

Publication number Publication date
ES2711639T3 (es) 2019-05-06
BR112013027279A2 (pt) 2016-09-20
CN103491786A (zh) 2014-01-01
US20140113823A1 (en) 2014-04-24
GB201107039D0 (en) 2011-06-08
US10206388B2 (en) 2019-02-19
TW201304679A (zh) 2013-02-01
UY34031A (es) 2012-11-30
EP2701518B1 (fr) 2018-11-14
BR112013027279B8 (pt) 2019-07-30
TW201637569A (zh) 2016-11-01
EP2701518A1 (fr) 2014-03-05
WO2012146889A4 (fr) 2013-01-03
CN103491786B (zh) 2018-05-22
BR112013027279B1 (pt) 2019-05-14
TWI677285B (zh) 2019-11-21
AR086183A1 (es) 2013-11-27
TWI684409B (zh) 2020-02-11

Similar Documents

Publication Publication Date Title
US9173397B2 (en) Formulation component
US10206388B2 (en) Formulation component
US20170055533A1 (en) Aromatic phosphate esters as agrochemical formulation component
KR102552658B1 (ko) 애쥬번트
US9456599B2 (en) Adjuvants
CN106212457B (zh) 配制品组分
CA2768093A1 (fr) Formulations

Legal Events

Date Code Title Description
DPE2 Request for preliminary examination filed before expiration of 19th month from priority date (pct application filed from 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12716512

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2012716512

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: DE

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112013027279

Country of ref document: BR

WWE Wipo information: entry into national phase

Ref document number: 14113678

Country of ref document: US

ENP Entry into the national phase

Ref document number: 112013027279

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20131023